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Oregon vacation rentals

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Top-rated vacation rentals in Oregon

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Cabin in Rhododendron
Cozy Mount Hood cabin with wood stove and hot tub
“Hütte Mount Hood” is an updated, classic cabin in a national forest on Mount Hood with campy vibes. Adorable set up with easy access in and out, but tucked away for a peaceful retreat. Comfortably set up to work remote or enjoy the seclusion of Mount Hood. Ample space for 4 guests with large outdoor area, hot tub and seating. Short drive to Government Camp, Timberline Resort, Ski Bowl, and Mt. Hood Meadows. Tons of hiking and outdoor activities nearby. ~45 min drive from PDX airport.
$164 per night
Cabin in Rhododendron
Klaus Haus-A cozy, modern retreat
This remodeled cabin is a beauty! It is architecturally unique with interesting lines, floor to ceiling windows, an open concept main floor, wood burning fireplace, and a king sized bed in the loft. This is a great home base for exploring all that Mt. Hood has to offer and a beautiful space to relax in afterwards!
$146 per night
Cabin in Rhododendron
Komorebi House-Modern Luxury in the Woods
Komorebi House is a modern one bedroom cabin in the Mt Hood National Forest. The design is inspired by travels to Japan and a love for the PNW. Komorebi combines luxury with all of the comforts of home to create the perfect place to unplug from the world and enjoy the simple elegance of a cabin-in-the-woods.
$185 per night

Oregon waterfront vacation rentals

Home in Rockaway Beach
Cozy 2 Bedroom Ocean front. Steps to beach access
$141 per night
Cabin in Rhododendron
River View Cabin - Cozy Cabin, Awesome Views,
$173 per night
Cottage in Tillamook
Heart of The Hill (Unit A) Oceanside oregon
$216 per night
Home in Sandy
Charming 1BR Riverfront Dog Friendly | Hot Tub
$241 per night

Oregon fishing vacation rentals

Cabin in Cottage Grove
Classy Comfortable Close in Creekside Cabin
$183 per night
Condo in Lincoln City
Beachfront, Hot Tub, Onsite Beach, 2 Stays Left!
$276 per night
Cabin in Joseph
Beautiful 2BR Lakefront Wallowa Lake | Hot Tub
$159 per night
Home in Florence
Contemporary 2BR Lakefront | Hot Tub | Dock
$235 per night

Vacation rentals with pools in Oregon

Home in Terrebonne
Cozy Three Story Lookout Tower
$299 per night
Condo in Lincoln City
Chic Oceanfront Condo - Top Floor - Fireplace!
$114 per night
Home in Terrebonne
Pointe of Blessing canyon golf course view retreat
$190 per night
Cabin in Rhododendron
Retro Modern Cabin-Seasonal Stream & HotTub-Dogs 👍
$288 per night

Your guide to Oregon

Welcome to Oregon

When you think of Oregon, you might immediately picture waterfalls in mossy forests, cyclists zipping around compact neighborhoods, and a culinary scene where nearly everything is labeled local and artisan. Really, that’s not far off the mark. The largest cities — the main metropolis of Portland, the smaller state capital Salem, and college town Eugene in the Willamette Valley — are only minutes away from farm country and protected wilderness areas; half the state, in fact, is covered in forest. Once you drive across the Cascade Range, scenic highways wind through the high deserts of central and eastern Oregon, where you’ll encounter ghost towns and geological wonders such as the Painted Hills and Smith Rock. Head south to spot bald eagles soaring overhead in the Klamath Basin and vintners welcoming you to lesser-known wineries around old gold-rush cities. Everywhere in between, it seems you’ll find a wild and scenic river to paddle and a picturesque trail to hike.

The best time to stay in a vacation rental in Oregon

Yes, Oregonians experience their fair share of rain — especially in the western half of the state. In places such as Portland, the Oregon Coast, and Willamette Valley, you can expect wet and temperate conditions from late fall through early spring, when drizzly mornings often give way to sunbreaks in the afternoons. Winter and early spring are also snow season in the popular ski areas around Mount Hood and Mount Bachelor, and cozy times for staying in one of the state’s many cabin rentals. All of that rain makes spring a particularly colorful time, when sprawling tulip fields blossom in dazzling shades and roses unfurl during century-old festivals. Summer is balmy, but usually not too humid, making it prime time for outdoor concerts and adventures in the rugged outdoors. Early fall is the sweet spot, when the weather remains crisp and the traffic becomes light on the state’s winding Scenic Byways and Scenic Bikeways.

Top things to do in Oregon

Crater Lake National Park

Take a collapsed volcano, fill it with remarkably blue water, and you have the deepest lake in North America — and the seventh-deepest lake in the world. It’s among the most iconic sights on the West Coast and certainly worthy of a road trip to southern Oregon. Depending on the season, you can drive or ski the scenic highway loop around the rim for magical views of Wizard Island, an ancient cinder cone that rises like an iceberg above the lake’s surface.

Columbia River Gorge National Scenic Area

A short ride east of Portland brings you into a dramatic canyon of basalt cliffs, where the Columbia River rushes past Multnomah Falls, the state’s tallest waterfall, along cool waterfront towns such as Hood River, and offers scenic overlooks galore. This is the United States’ largest national scenic area, famous for its waterfalls, hiking trails, and windsurfing.

WIllamette Valley wineries

More than 500 wineries dot the Willamette Valley, where tasting rooms feel more like low-key hangouts and families still operate many of the small-lot vineyards. The volcanic soils and temperate climate have made the valley the ideal environment for growing pinot noir, pinot gris, and chardonnay. Despite the young age of Oregon’s wine industry, the state’s vintages increasingly receive international acclaim.

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